My dad sent me and my brothers a letter once. In it, he said that he planned to die broke.
He failed in that goal. He left his wife in financial comfort for as long as she lives and each of us got a serious boost to our retirement accounts.
No wife...
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The problem with the whole idea of dying broke is you are BROKE and to be old and broke really sucks. It's a lot better to have a comfortable cushion and just realize somebody's going to enjoy it. Also, as one grows older, the scope of one's activities tends to shrink, causing one's wealth to increase and seeing that increase is enjoyable in itself.